Ethanol → Benzyl 3-aminobenzyl(methyl)carbamate

HRID 735653Notes

Reaction equation

HRID 735653 reaction equation
[CH3:1][N:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCO.O>[Fe].CC(O)=O>[NH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 57842906benzyl N-methyl-N-[(3-nitrophenyl)methyl]carbamate

Product 1

HCID 57842860Benzyl 3-aminobenzyl(methyl)carbamateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a refluxing solution of 60A (1.7 g, 5.8 mmol), EtOH (60 mL), water (15 mL) and AcOH (4 mL) was added portion-wise Fe powder (1.63 g, 29.0 mmol) over 30 min. The mixture was heated for 45 min. before cooling to ambient temperature and filtered through celite. Filtrate concentrated in vacuo to afford 60B (1.5 g, 95%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.25-1.41 (m, J=4.39 Hz, 3 H) 2.27 (s, 3 H) 2.61 (s, 2 H) 2.92 (s, 2 H) 4.22 (s, 2 H) 4.64 (s, 1 H) 6.84-7.56 (m, 12 H)

Workup

  1. temperatureThe mixture was heated for 45 min.
  2. filtrationfiltered through celite
  3. concentrationFiltrate concentrated in vacuo

Sources & evidence

ORD record
ord-bd30c7d78bf649b8950a4bc79eafa0c9
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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